The Best Sales Discovery Questions to Ask Your Prospects
At Anthony Cole Training Group, we often challenge salespeople to reflect on one simple but powerful question:
How good are you at getting your prospects to the point where they can’t stop thinking about the discussions you’re having with them?
This ability—getting into the prospect’s head and staying there—is one of the defining traits of top-performing salespeople. It all comes down to one key skill: discovery.
The Power of Discovery
Great salespeople don’t just pitch. They guide. They ask the right questions that lead prospects to realize, on their own, that they have a problem they need to solve, and that you’re the one who can help.
We call this approach engaging the prospect in the art of gradual self-discovery.
Here’s why it works: People can ignore you, but they can’t escape their own thoughts.
They might ignore your voicemail. They might not respond to your email. But if you’ve planted a meaningful idea in their mind—something they realize they need to address—it’s going to stick with them. Just like a restaurant you suddenly crave or a vacation you can’t stop thinking about, those thoughts are hard to shake.
That’s the goal: create that kind of mental traction.
How Do You Get to Great Sales Discovery Questions?
Top salespeople are naturally curious. They don’t push, they pull. They invite prospects into meaningful conversations by asking smart, thoughtful questions that dig deep.
Here are a few examples to guide your next conversation:
Why am I here?
When I called, why did you agree to meet with me?
You could’ve said no, but you didn’t… what’s going on?
What needs to happen today for this to be a valuable meeting?
What’s the most important thing for us to cover?
And as the conversation progresses:
How long has that been a problem?
What have you done to fix it?
When you brought it up with your current provider, what did they say?
What happens if this doesn’t get resolved?
What’s at stake for you? For your company?
Is this something you need to fix now, or can it wait?
Be Memorable
These sales discovery questions lead to powerful realizations. They create a space for honest conversation and help your prospect discover, through their own words, what’s not working, and what needs to change.
That’s how you become memorable. That’s how you earn the kind of mindshare that keeps you top of mind, even after the meeting ends.
Thanks for reading, and here’s to great conversations ahead.
Author:
Mark Trinkle, Chief Growth Officer
Anthony Cole Training Group
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